18494-67-2Relevant academic research and scientific papers
One-Pot Amide Bond Formation from Aldehydes and Amines via a Photoorganocatalytic Activation of Aldehydes
Papadopoulos, Giorgos N.,Kokotos, Christoforos G.
, p. 7023 - 7028 (2016/08/30)
A mild, one-pot, and environmentally friendly synthesis of amides from aldehydes and amines is described. Initially, a photoorganocatalytic reaction of aldehydes with di-isopropyl azodicarboxylate leads to an intermediate carbonyl imide, which can react with a variety of amines to afford the desired amides. The initial visible light-mediated activation of a variety of monosubstituted or disubstituted aldehydes is usually fast, occurring in a few hours. Following the photocatalytic reaction, addition of the primary amine at room temperature or the secondary amine at elevated temperatures leads to the corresponding amide from moderate to excellent yields without epimerization. This methodology was applied in the synthesis of Moclobemide, a drug against depression and social anxiety.
Catalytic chemical amide synthesis at room temperature: One more step toward peptide synthesis
Mohy El Dine, Tharwat,Erb, William,Berhault, Yohann,Rouden, Jacques,Blanchet, Jér?me
, p. 4532 - 4544 (2015/05/13)
An efficient method has been developed for direct amide bond synthesis between carboxylic acids and amines via (2-(thiophen-2-ylmethyl)phenyl)boronic acid as a highly active bench-stable catalyst. This catalyst was found to be very effective at room temperature for a large range of substrates with slightly higher temperatures required for challenging ones. This methodology can be applied to aliphatic, α-hydroxyl, aromatic, and heteroaromatic acids as well as primary, secondary, heterocyclic, and even functionalized amines. Notably, N-Boc-protected amino acids were successfully coupled in good yields with very little racemization. An example of catalytic dipeptide synthesis is reported.
AIBN-initiated metal free amidation of aldehydes using N-chloroamines
Vanjari, Rajeshwer,Guntreddi, Tirumaleswararao,Singh, Krishna Nand
supporting information, p. 351 - 356 (2014/01/06)
An efficient and environmentally benign amidation of aldehydes with N-chloroamines has been developed using AIBN as an initiator. This methodology offers a metal free and base free approach and is endowed with mild reaction conditions, high yields, and good functional group tolerance.
Direct amidation from alcohols and amines through a tandem oxidation process catalyzed by heterogeneous-polymer-incarcerated gold nanoparticles under aerobic conditions
Soule, Jean-Francois,Miyamura, Hiroyuki,Kobayashi, Shu
supporting information, p. 2614 - 2626 (2013/11/19)
We describe herein a highly elegant and suitable synthesis of amide products from alcohols and amines through a tandem oxidation process that uses molecular oxygen as a terminal oxidant. Carbon-black-stabilized polymer-incarcerated gold (PICB-Au) or gold/cobalt (PICB-Au/Co) nanoparticles were employed as an efficient heterogeneous catalyst depending on alcohol reactivity and generated only water as the major co-product of the reaction. A wide scope of substrate applicability was shown with 42 examples. The catalysts could be recovered and reused without loss of activity by using a simple operation. Gold standard: A highly efficient green method for amide synthesis from alcohols and amines catalyzed by gold nanoparticles stabilized by styrene-based copolymers has been developed (see scheme). Two catalysts have been used with high selectivity depending on the combination of substrates. These Au nanoparticle catalysts can be recovered and reused several times by simple operations. Copyright
Iron-catalyzed amidation of aldehydes with N-chloroamines
Porcheddu, Andrea,Luca, Lidia De
, p. 2949 - 2953,5 (2012/12/13)
A new direct conversion of aldehydes to amides has been realized, in the presence of iron(III) chloride as a catalyst and using tert-butyl hydroperoxide (TBHP) as an oxidant. Both aliphatic and aromatic aldehydes were successfully reacted with variously mono- and di-substituted N-chloroamines. The methodology has a wide substrate scope, uses cheap and easily available reagents and is characterized by short reaction times. Copyright
Iron-catalyzed amidation of aldehydes with N-chloroamines
Porcheddu, Andrea,Luca, Lidia De
, p. 2949 - 2953 (2013/01/15)
A new direct conversion of aldehydes to amides has been realized, in the presence of iron(III) chloride as a catalyst and using tert-butyl hydroperoxide (TBHP) as an oxidant. Both aliphatic and aromatic aldehydes were successfully reacted with variously mono- and di-substituted N-chloroamines. The methodology has a wide substrate scope, uses cheap and easily available reagents and is characterized by short reaction times. Copyright
One-pot synthesis of amides from aldehydes and amines via C-H bond activation
Cadoni, Roberta,Porcheddu, Andrea,Giacomelli, Giampaolo,De Luca, Lidia
supporting information, p. 5014 - 5017,4 (2012/12/12)
A one-pot synthesis of amides from aldheydes with N-chloroamines, prepared in situ from amines, has been developed. Both aliphatic and aromatic aldehydes and many types of mono- and disubstituted amines are tolerant in this transformation. This cross-coupling reaction appears simple and convenient, has a wide substrate scope and makes use of cheap, abundant, and easily available reagents.
One-pot synthesis of amides from aldehydes and amines via C-H bond activation
Cadoni, Roberta,Porcheddu, Andrea,Giacomelli, Giampaolo,De Luca, Lidia
supporting information, p. 5014 - 5017 (2013/01/15)
A one-pot synthesis of amides from aldheydes with N-chloroamines, prepared in situ from amines, has been developed. Both aliphatic and aromatic aldehydes and many types of mono- and disubstituted amines are tolerant in this transformation. This cross-coupling reaction appears simple and convenient, has a wide substrate scope and makes use of cheap, abundant, and easily available reagents.
Catalytic transamidation reactions compatible with tertiary amide metathesis under ambient conditions
Stephenson, Nickeisha A.,Zhu, Jiang,Gellman, Samuel H.,Stahl, Shannon S.
experimental part, p. 10003 - 10008 (2009/12/08)
The carbon-nitrogen bond of carboxamides is extremely stable under most conditions. The present study reveals that simple zirconium- and hafnium-amido complexes are highly efficient catalysts for equilibrium-controlled transamidation reactions between sec
[Bis(2-methoxyethyl)amino]sulfur Trifluoride, the Deoxo-Fluor Reagent: Application toward One-Flask Transformations of Carboxylic Acids to Amides
White, Jonathan M.,Tunoori, Ashok Rao,Turunen, Brandon J.,Georg, Gunda I.
, p. 2573 - 2576 (2007/10/03)
The use of the Deoxo-Fluor reagent is a versatile method for acyl fluoride generation and subsequent one-flask amide coupling. It provides mild conditions and facile purification of the desired products in good to excellent yields. We have explored the utility of this reagent for the one-flask conversion of acids to amides and Weinreb amides and as a peptide-coupling reagent.
